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10 Romantic films with bittersweet endings

BY Ben Stanley

1st Jan 2015 Film & TV

10 Romantic films with bittersweet endings

Love can be tough and with Valentine's Day rapidly approaching, it can be even harder. Here are ten films that show how love can be amazing, disastrous and, sometimes, a mixture of both.

1. 500 days of Summer


“You should know up front that this is not a love story”

Forget the conventional "girls love romance" and "guys hate commitment" as these ideals are spun upside down when Tom, a hopeless romantic, tries to win over the relationship-phobe, Summer.

Tom's continuous passion towards Summer isn’t enough to change her ideals on love though, which could make audiences hate her but we know that love isn’t always reciprocated. Tom fell in love with the idea of Summer but she didn’t want that, which only led to heartbreak.

As Tom tries to let go of his belief in fate, he meets a girl at an interview, Autumn. A sweet ending to an emotional roller coaster of a film but like the seasons, it's hard for Autumn to top Summer.


2. Brokeback Mountain


A beautiful and heartfelt journey of homosexual love during a time that found it unacceptable. What begins as a friendship between two sheepherders, Ennis and Jack, turns into a love affair that's a risk from the beginning.

We explore the lives of both men after their affair, seeing them both marry women and have children but also the foreseen deterioration of those forced relationships. The men, however, still meet for secret trips—the only way that they can be together.

Following a falling out between the two men, Ennis discovers through a returned postcard that Jack has passed away. The impact of the death is powerful enough but the fact that the pair were unable to be together in a space that wasn’t secret is truly devastating. The theme of forbidden love has never been as true as in Jack and Ennis' romance.


3. La La Land 

Being attracted to appearances is easy but falling for someone because of their sheer passion and talent is something special. Mia and Sebastian find themselves infatuated with each other throughout this classically styled contemporary musical but each with their own specific dreams, making it hard to find the middle ground.

Towards our conclusion, we fast forward five years and see that both our leads have achieved their personal dreams but not with each other. Mia is a successful Hollywood star with a husband and child. Sebastian finally opened his own jazz club, called "Seb’s"—the name and logo that Mia has previously suggested.

The true impact of their separate lives comes in a dream sequence from the perspective of Mia, showing what could have been. A devastatingly beautiful montage of sequences that have you wanting to reverse the film to its beginning.


4. Grease


Summer romances are amazing experiences that come to an end far too soon, that is until Sandy unintentionally ends up at the same school as summer lover, Danny. On paper this should be perfect but in reality they are very different people with opposite friendship groups.

This high-school musical follows a "will they/won't they" trope, constantly putting the pair in negative situations but what for? Is it true love or just a summer fling? 

The couple end up riding into the sunset together (literally in a flying car towards the sun) but this is after they change their styles for one another. Finding the middle ground is healthy in a relationship but becoming something you're not for your partner is less romantic and rather sad.


5. The Breakup 

Image via confusedsandals

The title clearly indicates the direction of this 2006 romantic comedy: relationships not working and coming to an end. Even with the impending doom, we're rooting for Brooke and Gary to come to terms with their issues but they go their separate ways, advancing where they couldn’t together.

As the story concludes, we witness the pair bump into each other, years after their break up. There's a sense of reconciliation between the two, giving a glimmer of hope that the exes can be friends but not the couple that they once were.


6. Her 

Theodore’s failed relationship has pushed him into isolated depression but that begins to change after he purchases an advanced operating system, Samantha. We watch as they bond and seemingly fall in love.

Scarlett Johansson’s vocal performance gifts the computer with a sense of humanity, tricking both Theodore and the audience into believing that this unconventional love between man and machine is real, but when he discovers that Samantha is simultaneously speaking to thousands of people and is in love with hundreds of them, he is crushed.

It’s complex to determine whether Samantha should be seen as a cheat since she's an operating program that has specifically been designed for this. We close with Theodore and his friend, Amy, watching the sunrise, indicating that this experience has made him stronger, yet the love for Samantha was real and, sadly, gone.

Rooting for a romance between a man and an operating system sounds wrong but the performances throughout made it feel so right.


7. Ruby Sparks

A traditional romance often begins when boy meets girl, but this isn’t that straightforward. Calvin, a successful writer in a creative slump, starts to write about Ruby, a fictional character that he's in love with. By magic, Ruby appears in the flesh at Calvin’s home. His words have become reality; whatever Calvin writes about Ruby, comes true.

Calvin starts to change Ruby, first in humorous and small ways but they quickly turn controlling. His fragile ego gets in the way of the natural build between the two (as "natural" as love between a man and his creation can get) with each new addition changing the traits he loved.

Calvin realises how wrong playing God is, and writes one last page, freeing Ruby from his control. 


8. The Notebook

Nicholas Sparks has a limitless library of successful love stories but few have enjoyed the cultural impact of The Notebook.

Taking place in the past and the present, we learn about the love between Allie and Noah, two lovers from different social classes. Allie’s family is disgusted by the idea of Noah and will do anything to prevent them being together—from moving town to hiding love letters, but Noah doesn’t give up and eventually wins her back.

It's revealed that the present elderly version of Allie has dementia and doesn’t remember much about her relationship with Noah. This is additionally hard to see as the elderly Noah remembers every detail but Allie anticipated her memory issues and wrote down their love story with instructions for Noah so that their love would never die.

"Read this to me, and I'll come back to you”


9. Titanic

Image via pluggedin

Not many romance films are based on real life disasters but this 1997 Oscar-winner follows a couple who fall in love during the Titanic’s unfortunate maiden journey.

Rose and Jack are teenagers from incredibly different backgrounds but they click as if it was fate. Yet the unfortunate side effect of their meeting is that their ship is sinking after colliding with an iceberg.

The Titanic is split in two with many of the passengers at the bottom of the sea. There's still somehow hope for Jack and Rose—that’s until they're thrown into the freezing sea with only a wooden panel to float on. Jack assures Rose that there's only room for one and sacrifices himself so that she can survive.

Jack’s sacrifice is one of the film's most iconic moments and as devastating as it is, it shows that his love was true. Rose’s devotion can be questioned as she probably could have budged up a little to fit Jack on…


10. West Side Story

Based on Romeo and Juliet, this gripping musical tackles race and gang culture in 1960s New York City. "The Jets" are a white American gang whereas "The Sharks" are a gang of Puerto Ricans, neither see eye to eye. This complex relationship gets even tougher when Tony, a member of "The Jets" falls for Maria, sister to the "The Sharks" leader.

Even with everything against them, the couple continues to pursue their forbidden love. As they finalise their escape, Tony is shot dead in front of Maria. As she cradles her dying man, the gangs appear to fight once more but are stopped as Maria makes them all accountable for all the deaths.

A musical based on Romeo and Juliet was never going to end happily ever after but we were so very close.



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